Treatment of damaged hair with methylol compounds

ABSTRACT

Cosmetic composition for use in treating damaged hair. The composition comprises, as the active component a methylol compound of the formula:   IN A SUITABLE COSMETIC CARRIER, IN WHICH FORMULA: X represents either an oxygen atom or a sulfur atom or an NH group; R and R&#39;&#39; are identical or different and represent either a hydrogen atom or a lower alkyl radical; and R1 and R2 represent either a methyl hydroxy group or a methyl alkoxy group, e.g. methyl alkoxy wherein the alkoxy contains up to five carbon atoms or more. Typically the methylol compound is N,N&#39;&#39;-dihydroxymethyl glyoxalurea or N,N&#39;&#39;-dihydroxymethyl glyoxalthiourea. The composition is applied at an acid pH and is advantageously made up in solid form for mixing with water or water-and-alcohol solutions when used. The compositions are used by impregnating the hair with a mixture thereof and water or water-and-alcohol solution followed by drying with heat.

United States Patent Kalopissis et al.

[451 June 27, 1972 [54] TREATMENT OF DAMAGED HAIR WITH METHYLOLCOMPOUNDS Inventors: Gregoire Kalopissis; Henri Philippe De Beaulieu,both of Paris; Jean-Louis Abegg, Le Perreux; Giuliana Ghllardi, Paris,all of France [73]. Assignee: Societe anonyme dite:

France Filed: Aug. 19, 1969 Appl. No.2 851,473

LOreal, Paris,

Foreign Application Priority Data Aug. 26, 1968 Luxembourg ..56768 U.S.Cl ..l32/7, 8/ 1 27.5 1 424/47, 424/70, 424/71 Int. Cl ..A6lk 7/06, A45d7/04 Field of Search ..424/47, 70, 71;8/127.6, 127.5], 8/1 16.2; 132/7[56] References Cited UNITED STATES PATENTS 3,209,010 9/1965 Gagliardiet al ..8/1l6.2 X 3,350,162 10/1967 Beck ....8/1 16.2 X 3,442,905 5/1969Primary Examiner-Albert T. Meyers Assistant Examiner-Vera C. ClarkeAttorney-Cushman, Darby & Cushman l-lerbes et al. ..8/1 16.2 X

[5 7] ABSTRACT Cosmetic composition for use in treating damaged hair.The composition comprises, as the active component a methylol compoundof the formula:

Typically the methylol compound is N,N'-dihydroxymethyl glyoxalurea orN,N'-dihydroxymethyl glyoxalthiourea.

The composition is applied at an acid pH and is advantageously made upin solid form for mixing with water or water-and-alcohol solutions whenused. The compositions are used by impregnating the hair with a mixturethereof and water or water-and-alcohol solution followed by drying withheat.

5 Claims, No Drawings The present invention relates to a new.cosmeticcomposition intended for restoration of human hair which haspreviously been more or less severely damaged.

it is .known that there are numerous factors which tend to degrade thekeratin of the hair. Thus atmospheric agents such as sun and sea water,or chemical treatments accompanying perrnanents and bleaching operationsinvolve a certain breakdown of .the hair keratin. This degredation mostoften causes a significant loss of brilliance and of the aestheticqualities of the hair. Damaged hair also becomes brittle and breakseasily, which can cause a rapid reduction of the total bulk of the hair.

, Treatment of the hair to increase mechanical resistance and elasticityhas already been suggested, namely with use of compositions whichcontain polycondensable. N-methylol nitro compounds. These compoundshave the characteristic of being able, when acted upon by acid catalystsand heat, to polymerize within the keratin, giving rise to a resin thatcan strengthen the hair. In addition, these compounds can be fixed tothe keratin by their methylol function and thus create new crosslinkages of the keratin fiber,- which also reinforces the hair.

It has been shown, however, that most of the known and used methylolcompounds have the disadvantage of being relatively difficult todissolve in water, which complicates their use in aqueous cosmeticcompositions that are to be utilized as hair impregnants.

The present invention relates to cosmetic compositions containing one ormore polycondensable methylol compounds as the base or essentialcomponent, which reinforce the keratin and moreover present theadvantage of being much more soluble in water and in water-and-alcoholsolutions than are the methylol compounds which have been previouslydescribed for use in this field of application.

The present invention relates to a cosmetic composition characterized inthat it contains at least one compound of the formula:

in a suitable cosmetic carrier, in which formula X represents either anoxygen atom or a sulfur atom or an NH group;

R and R are identical or different and represent either a hydrogen atomor a lower alkyl radical; and

R and R represent either a methyl hydroxy group or a methyl alkoxygroup, e.g., methyl alkoxy wherein the alkoxy contains up to five carbonatoms or more.

In a preferred embodiment of the invention, the cosmetic carrier of thecomposition is a solid carrier which offers good solubility in water andin water-and-alcohol solutions. The preparation of the composition as asolid is made possible by the substantial solubility of the activecompounds which permits them to be very readily dissolved by the user atthe time of application. The solid form of the composition isadvantageous, because the composition can be stored in this way to avoidthe risk of degradation of the active compounds which could occur in thecourse of extended storage of these compounds in aqueous solution.

In another embodiment, the composition of the invention is prepared asan aqueous or water-and-alcohol solution (e.g., water/ ethanol orwater/isopropanol) of the methylol compound described above, in aconcentration ranging between 0.5 and 12 percent by weight of the activecomponent or components. The composition of the invention can also beprepared as a cream, a gel or an aerosol.

According to a specific embodiment, the composition may also contain anacid-reacting compound which allows its pH to be brought to a valuebetween 1.5 and 5.

Among the active compounds that can be utilized according to theinvention, there may be mentioned N,N -dihydroxymethyl glyoxalurea ofthe formula:

and N,N-dihydroxymethyl glyoxalthiourea of the formula:

The composition of the invention may also contain conventionalingredients such as swelling agents, surfactants, penetration agents, ordyes, perfumes, and cosmetic resins.

The present invention is also concerned with a process for treating thehair, characterized in that the hair is impregnated with a compositionsuch as described above, in liquid or fluid form, the hair also beingimpregnated with an acid solution if the composition itself does nothave an acid pH, followed by drying the hair with the application ofheat, the hair being optionally rinsed before drying.

To facilitate the effecting of the treatment described above, it ispossible,- for example, to formulate the cosmetic composition in liquidor fluid form at the moment of application to the hair. Thus, a solidcomposition according to the invention and comprising the methylolcompound and solid carrier can be mixed with water or awater-and-alcohol solution with acid pH to make a lotion or the likewhich is applied to the hair directly after mixing.

ln a preferred embodiment of the invention, the treatment processdescribed above is effected along with a hair-curling operation, thehair being rolled up after impregnation with the composition on curlerrolls and dried by the application of heat.

The advantages of using the compositions of the invention in the mannerdescribed herein are that, even in the case of hair that has beensubstantially damaged, there is attained a curl that is of excellentquality, the hair regaining its original softness, sheen and liveliness.

For a better understanding of the invention, the following examples ofcompositions according to the invention and methods of using the sameare presented, it being understood that these are given for purposes ofillustration and are not intended to be in any way limiting:

EXAMPLE I Oleic alcohol l0 moles 0.5. (Brij 96) 23 g Paraffin oil 22 gN,N'-dihydroxymethyl glyoxalthiourea 0.2 g Perfume 0.2 g Water 55 gEXAMPLE 2 A gel having the following composition is which has beenbleached, just before setting it:

applied to hair Oleic acid 10 moles 0.5. 27 g Paraffin oil 23 gN.N'-dihydroxymethyl glyoxalurea 0.5 g Pure acetic acid q.s.p. pH 3.5Water 50 cc with the application of heat.

2. The process of claim 1 wherein the acid in said aqueous acid solutionis selected from the group consisting of acetic, citric and phosphoricacid.

3. The process of claim 1 wherein said damaged hair is impregnated withan aqueous acid solution having a pH of 1.5-5 prior to impregnating saidhair with said composition.

4. The process of claim 1 which also includes rolling up said hairimpregnated with said composition on curlers prior to drying said hair.

5. The process of claim 1 which also includes rinsing said hairsubsequent to impregnating the same with said composition and prior todrying said hair.

2. The process of claim 1 wherein the acid in said aqueous acid solutionis selected from the group consisting of acetic, citric and phosphoricacid.
 3. The process of claim 1 wherein said damaged hair is impregnatedwith an aqueous acid solution having a pH of 1.5-5 prior to impregnatingsaid hair with said composition.
 4. The process of claim 1 which alsoincludes rolling up said hair impregnated with said composition oncurlers prior to drying said hair.
 5. The process of claim 1 which alsoincludes rinsing said hair subsequent to impregnating the same with saidcomposition and prior to drying said hair.